Or is this better? I cannot find guidance anywhere that addresses these with any specificity. All I'm told to do is recast. Surely, there has to be an answer to these.

Joe said, "My grandfather once owned and operated a $60-to-70-million-a-year business empire." (Or should I repeat "million," as in "a $60-million-to-70-million-a-year business empire"?) I think that using suspended hyphenation is jarring to the reader (e.g., "a $60-million- to 70-million-a-year business empire").

Would anybody concur that forgoing those distracting hyphens would be the way to go? It's less cluttered and cleaner. I know there are better ways to write these, but I can't, because they're direct quotes. See below.
(BTW, The AP Stylebook doesn't address this.)

Joe said, "My grandfather once owned and operated a $60 million to 70 million a year business empire."

Mike said, "The figures represented a $100,000 to 150,000 a year increase in revenues."

Horatio said, "The monetary gains reflected a 10 to 20 percent a year increase in sales."

Your hyphens are fine. In each case both forms are fine. However, if the context would allow anyone to think that $10 means ten dollars, you are better off spelling it out as $10,000. Note too that anytime you have more than two hyphens in an expression it begins to look ugly and is worth rewriting:

The figures represented an annual increase in revenues of $10,000 to $20,000.

The New York Times Manual of Style and Usage gives the following examples:

$2.5 million investment

a $10-to-11-billion increase
(Note that there's no dollar sign before the number 11.)

a $2-million-a-year job

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Where are you getting this? Because I am (almost!) certain it is wrong, subject to the proviso that the Times recently revised its stylebook. Since I am a New York Times editor, I should know this automatically, but I'm only almost sure that I do. The correct NY Times style is: $2.5-million investment ($2.5 million here is a compound modifier and requires the hyphen.) A $10-billion-to-$11-billion increase. The rationale is that while it's a wildly implausible possibility, it is nevertheless possible that the increase was somewhere between ten dollars and eleven billion dollars. And the sentence as you write it states exactly that. So to avoid any possibility of confusion, one must use $10 billion and not $10 in the compound modifier (along with hyphens). Finally, the Times would counsel to avoid the awkward compound modifiers altogether, and write: "Revenue was forecast to increase from $10 billion to $11 billion next year." Hope this helps.

If this is dialogue in a fictional story, I would suggest it's a bit flat. Try instead, "My grandfather once owned a business empire that raked in tens of millions of dollars a year! How much money do you make? … That's what I thought! Fuck you, and don't dis my gramps again."

Please confirm. So for quoted written dialogue, we should forgo hyphenation—especially for compound-modifying phrasal adjectives—unless of course we're dealing with the numbers 21–99 (which inherently require hyphenation).

For instance, we omit hyphens in dialogue (not narratives) when we have something akin to the following:

Please confirm. So for quoted written dialogue, we should forgo hyphenation—especially for compound-modifying phrasal adjectives—unless of course we're dealing with the numbers 21–99 (which inherently require hyphenation).

For instance, we omit hyphens in dialogue (not narratives) when we have something akin to the following:

Mike said, "The four year old was misbehaving."

In a narrative we would write:

The four-year-old was misbehaving. (With hyphens.)

Correct?

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I don't think the issue is hyphenation. I'd write: Mike said, "The four-year-old was misbehaving."

The issue I wanted to emphasize is, how do you say "$60-70 million"? Look at the three examples I gave above. They're all different (and the issue, once again, isn't the hyphenation). Which would Joe say, verbally? I think it's important, in dialogue, to write it the way the character would say it.

I think you are obsessing way too much over this stuff, unless you are writing journalism or an essay or some such other pedant-filled crap. If you're writing fiction, do what you want. Read James Joyce, Jack Kerouac, Cormac McCarthy, Roberto Bolaño and others who famously had sentences that ran on for pages without correct punctuation or even without punctuation at all. If your concern is fiction writing, then forget about proper grammar, especially idiocies like compound modifiers and hyphens.